Windward 21 by Chesapeake Marine Design

Daysailer/Cuddy Cruiser

Length overall21'6.4 m
Beam6' 9"2.06 m
Draft3'0.91 m
Draft (cb up)1' 4"0.41 m
Ballast weight1200 lbs544 kg
Sail area156 sq. ft.14.49 m2
Hull construction Plywood
See also Windward 17Windward 24



WINDWARD 21 is based on the Seaside Bateaux once common working craft behind the barrier islands of Maryland's Atlantic coast. These boats were noted for their load capacity and speed under sail for a client who I designed her wanted a daysailer with a large and simple overnight cockpit .... accommodations under a boom .... She is stable and will ...many friends and farmily ....

Estimated cost for quality construction materials (not including power or sails) is $12000. This cost includes a high level of outfit and finish you can be proud of after putting the effort into building this fine boat.


See also

Design Length Beam Sail area Engine power Compare
Windward 17 by Chesapeake Marine Design
Daysailer/Beach Cruiser
5.18 m
1.52 m
106 sq. ft.
9.85 m2
Windward 24 by Chesapeake Marine Design
Daysailer / Camp cruiser
7.32 m
8' 6"
2.59 m
280 sq. ft.
26.01 m2

Boats about same size as Windward 21

  John's Sharpie
A Lightweight, Fast-Sailing Sharpie

LOA: 18'/5.51 m   compare
6 M Whaler   6 M Whaler
A clinker built double ender in the traditional Navy style

LOA: 19' 8"/5.99 m   compare

Questions? Suggestions? Contact us at: